1. Field of the Invention
The cephalosporins of the present invention in general possess the usual attributes of such compounds and are particularly useful in the treatment of bacterial infections.
2. Description of the Prior Art
U.K. Pat. No. 1,399,086 disclosed antibiotic compounds of the general formula ##STR2## (wherein R.sup.U is phenyl; naphthyl; thienyl; furyl, benzothienyl; benzofuryl; pyridyl or any of these groups substituted by halo (chloro, bromo, iodo or fluoro), hydroxy, lower alkyl, nitro, amino, loweralkylamino, diloweralkylamino, lower alkanoyl, lower alkanoylamino, lower alkoxy, lower alkylthio or carbamoyl; R.sup.b is lower alkyl; cycloalkyl containing 3-7 carbon atoms; carbocyclic or heterocyclic aryl lower alkyl or any of these groups substituted by hydroxy, carboxy, exterified carboxy, amido, cyano, alkanoyl, amino, substituted amino, halogen or lower alkoxy; and Y is selected from acetoxy; a group of formula ##STR3## where R.sup.d and n are as defined in claim 19; a group of formula --SW where W is thiadiazolyl, diazolyl, triazolyl, tetrazolyl, thiazolyl, thiatriazolyl, oxazolyl, oxadiazolyl, benzimidazolyl, benzoxazolyl, triazolopyridyl, purinyl, pyridyl or pyrimidyl; an alkylthio group containing 1-4 carbon atoms; a group of formula --O.CO.R.sup.9 where R.sup.9 is an alkyl or alkenyl group containing 2-4 carbon atoms; the group --O.CO.NH.(CH.sub.2).sub.m D wherein m is an integer of from 1-4 and D is chlorine, bromine, iodine or fluorine; and azido) and non-toxic salts and esters thereof. Methods for the preparation of the starting acids used to form the 7-substituent, including their separation into syn and anti isomers, are also described therein and in U.K. Pat. No. 1,404,221.
Presently issued U.S. Pat. Nos. 3,966,717 and 3,971,778 (with many nucleophilic substituents) contain at least part of the disclosure of U.K. Pat. No. 1,399,086 as does U.S. Pat. No. 3,974,153. See also Farmdoc abstracts 17270X and 19177X and 63415X (which also contains thiol substitution).
U.S. Pat. No. 3,974,153 claims compounds of the formula ##STR4## wherein R.sup.1 is furyl, thienyl or phenyl; and R.sup.a is C.sub.1-4 alkyl, C.sub.3-7 cycloalkyl or phenyl; and a physiologically acceptable salt thereof.
With reference to cephalosporins in which the acetoxy group in the 3-methyl substituent has been displaced by a thiol see U.S. Pat. No. 3,741,965 for a review of the older art.
For examples of publications in the scientific literature see Ryan et al., Antimicrobial Agents and Chemotherapy, 9, 520-525 (1976) and O'Callaghan et al., ibid., 9, 511-519 (1976) and Norby et al., ibid., 9, 506-510 (1976) regarding cefuroxime and Leitner et al., ibid., 10(3), 426-435 (Sept. 1976) regarding BL-S786.
In U.S. Pat. No. 3,907,786 claim 1 reads:
An acid having the formula ##STR5## or a nontoxic, pharmaceutically acceptable salt thereof.
One definition of R is tautomeric thus: ##STR6##
The latter can of course be written as ##STR7##